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New Hot Paper Comments

By Prof. Dr. Norbert Krause

ESI Special Topics, November 2002
Citing URL - http://www.esi-topics.com/nhp/comments/november-02-NorbertKrause.html

Prof. Dr. Norbert Krause answers a few questions about this month's new hot paper in the field of Chemistry


From •>>November 2002

Field: Chemistry
Article Title: "Recent advances in catalytic enantioselective Michael additions"
Authors: Krause, N;Hoffmann-Roder, A
Journal: SYNTHESIS-STUTTGART
Volume: (2) 171-196 FEB 2001
Page: 
Year: FEB 2001
* Univ Dortmund, D-44221 Dortmund, Germany.
* Univ Dortmund, D-44221 Dortmund, Germany.

ST:  Why do you think your paper is highly cited?

The paper is the most recent and comprehensive review on enantioselective Michael addition reactions carried out with catalytic amounts of both a transition metal and a chiral ligand. The method is used by many research groups for the stereoselective synthesis of chiral target molecules, in particular natural products and pharmaceutically active compounds. The unique feature of our review is that it covers all important transition metals (copper, nickel, rhodium, lanthanides, etc.) and even pure "organocatalytic" (metal-free) reactions, so that it appeals to many more researchers than other reviews which are specialized to only one metal.

ST:  Does it describe a new discovery or new methodology that’s useful to others?

This field is very "hot" right now, and new chiral ligands and procedures for catalytic enantioselective Michael additions appear almost every week. Since the publication of our review, I have collected over 100 new papers in the field! The most important advantage of the method (from my point of view) is that it can be used reliably for the synthesis of new, previously unknown products—even by "outsiders" who do not have any knowledge of the subtleties of the catalytic systems. Just a few years ago, a tedious screening of ligands and reaction conditions had to be carried out for every new substrate.

ST:  What were some of the circumstances that led you to do this research?

We are specialists in the use of organocopper compounds in organic synthesis, and have recently begun to use copper-catalyzed enantioselective Michael additions. Consequently, we know the literature concerning copper as catalyst metal rather well, and it was fascinating to learn how many interesting methods have recently been developed by using other transition metals. We will now also start to use also rhodium-catalyzed enantioselective Michael additions in our own research.

ST:  Could you summarize the significance of your paper in layman’s terms?

Many highly active drugs exist in two forms: object and mirror image. Usually, the human organism interacts differently with these two forms ("enantiomers"); one has the desired pharmacological activity, whereas the other is inactive or even harmful. A nice comparison is the human hand: a right glove does only fit to the right hand, not to the left. For this reason, it is very important to develop methods that allow for the synthesis of one enantiomer of these target molecules only ("enantioselective reaction"). The "Michael reaction" (named after the American chemist Arthur Michael) can be used towards this purpose, but only when being carried out in the presence of a transition metal (for example copper) and another molecule (chiral ligand). For economical and environmental reasons, it is highly desirable to use only very small amounts of these auxiliaries; such reactions are called "catalytic". Thus, the catalytic enantioselective Michael addition is ideal for the synthesis of drugs and other important target molecules.End

Prof. Dr. Norbert Krause
Dortmund University, Organic Chemistry II, 
D-44221 Dortmund, Germany

ESI Special Topics, November 2002
Citing URL - http://www.esi-topics.com/nhp/comments/november-02-NorbertKrause.html

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